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WO1991013846A1 - 1,1,2,2,3,3-hexafluorocyclopentane et son utilisation dans des compositions et des procedes de nettoyage - Google Patents

1,1,2,2,3,3-hexafluorocyclopentane et son utilisation dans des compositions et des procedes de nettoyage Download PDF

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Publication number
WO1991013846A1
WO1991013846A1 PCT/US1991/000470 US9100470W WO9113846A1 WO 1991013846 A1 WO1991013846 A1 WO 1991013846A1 US 9100470 W US9100470 W US 9100470W WO 9113846 A1 WO9113846 A1 WO 9113846A1
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WO
WIPO (PCT)
Prior art keywords
azeotrope
composition
weight percent
carbon atoms
hexafluorocyclopentane
Prior art date
Application number
PCT/US1991/000470
Other languages
English (en)
Inventor
Douglas Robert Anton
Original Assignee
E.I. Du Pont De Nemours And Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1991013846A1 publication Critical patent/WO1991013846A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02803—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/02—Monocyclic halogenated hydrocarbons
    • C07C23/08—Monocyclic halogenated hydrocarbons with a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5081—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/26—Cleaning or polishing of the conductive pattern

Definitions

  • This invention relates to halogen substituted hydrocarbon compounds, their compositions and uses, and more particularly to fluorine-substituted hydrocarbons, their mixtures with solvents such as ethanol or methanol, and the use thereof for cleaning solid surfaces.
  • Boiling point, flammability and solvent power can often be adjusted by preparing mixtures of solvents.
  • Azeotropic compositions exhibit either a maximum or minimum boiling point and do not fractionate upon boiling. These characteristics are also important in the use of the solvent compositions in certain cleaning operations, such as removing solder fluxes and flux residues from printed circuit boards. Preferential evaporation of the more volatile components of the solvent mixtures, which would be the case if the mixtures were not azeotropes, or azeotrope-like, would result in mixtures with changed compositions which may have less desirable properties (e.g. lower solvency for contaminants such as rosin fluxes and/or less inertness toward the substrates such as electrical components) . Azeotropic characteristics are also desirable in vapor degreasing operations where redistilled material is usually used for final rinse-cleaning.
  • the vapor defluxing or degreasing system acts as a still.
  • the solvent composition exhibits a constant boiling point (i.e. is an azeotrope or is azeotrope- like) fractionation will occur and undesirable solvent distribution may act to upset the safety and effectiveness of the cleaning operation.
  • a number of azeotropic compositions based upon halohydrocarbons containing fluorine have been discovered and in some cases used as solvents for the removal of solder fluxes and flux residues from printed circuit boards and for miscellaneous vapor degreasing applications.
  • 2,999,815 discloses the azeotrope of 1,1,2-trichloro-l,2,2- trifluoroethane with acetone;
  • U.S. Patent No. 3,903,009 discloses a ternary azeotrope of 1,1,2-trichloro-l,2,2- trifluoroethane with nitromethane and ethanol;
  • U.S. Patent No. 3,573,213 discloses an azeotrope of 1,1,2- trichloro-1,2,2-trifluoroethane with nitromethane;
  • 3,789,006 discloses the ternary azeotrope of 1,1,2-trichloro-l,2,2-trifluoroethane with nitromethane and isopropanol
  • U.S. Patent No. 3,728,268 discloses the ternary azeotrope of 1,1,2-trichloro-l,2,2- trifluoroethane with acetone and ethanol
  • U.S. Patent No. 2,999,817 discloses the binary azeotrope of 1,1,2- trichloro-1,2,2-trifluoroethane and methylene chloride
  • U.S. Patent No. 4,715,900 discloses ternary compositions of trichlorotrifluoroethane, dichlorodifluoroethane, and ethanol or methanol.
  • solvent compositions which have proven useful for cleaning contain at least one component which is a halogen-substituted hydrocarbon containing chlorine, and there have been concerns raised over the ozone depletion potential of halogen- substituted hydrocarbons which contain chlorine. Efforts are being made to develop compositions which may at least partially replace the chlorine containing components with other components having lower potential for ozone depletion. Azeotropic compositions of this type are of particular interest.
  • This invention provides a novel fluorohydrocarbon compound, 1,1,2,2,3,3-hexafluoro-cyclopentane, and mixtures thereof with miscible solvents such as alcohols (e.g. methanol, ethanol, isopropanol, etc.), ethers (e.g. tetrahydrofuran, etc.), esters, ketones (e.g. acetone) , nitromethane, and halogenated hydrocarbons (e.g. methylene chloride, 1,l,2-trichloro-l,2,2- trifluoroethane, dichlorodifluoroethane, trans-1,2- dichloroethylene, etc.).
  • miscible solvents such as alcohols (e.g. methanol, ethanol, isopropanol, etc.), ethers (e.g. tetrahydrofuran, etc.), esters, ketones (e.g. acetone) , nitromethane, and hal
  • an azeotrope or azeotrope-like composition comprising an admixture of effective amounts .of 1,1,2,2,3,3- hexafluorocyclopentane and an alcohol selected from a group consisting of methanol and ethanol and, more specifically, an admixture of either about 69 weight percent 1, 1,2,2,3,3-hexafluorocyclopentane and about 31 weight percent methanol, or about 75 weight percent 1,1,2,2,3,3-hexafluorocyclopentane and about 25 weight percent ethanol.
  • a novel fluorohydrocarbon compound, 1,1,2,2,3,3- hexafluorocyclopentane is provided in accordance with this invention.
  • the designation of this compound in conventional nomenclature for halogen-substituted hydrocarbons containing fluorine is C456ff.
  • C456ff may be prepared by mixing together 1,2-dichloro-hexafluoro- cyclopent-1-ene (available commercially) , an alkali metal acetate, Pd on carbon (a commercially available catalyst) , and excess hydrogen gas and reacting the mixture at a temperature in the range of about 0°C to
  • the reaction can be carried out in a pressure vessel such as a Parr shaker or an autoclave.
  • a pressure vessel such as a Parr shaker or an autoclave.
  • the crude product is filtered to remove catalyst, washed with water to remove acetic acid, treated with magnesium sulfate to remove excess water, then distilled to give pure C4356ff with a one degree boiling point range.
  • C456ff is a liquid under ambient conditions and is considered useful as a solvent which can be employed for cleaning contaminants from solid substrates.
  • compositions suitable for use in cleaning operations can be prepared which comprise a mixture of C 56ff with one or more compounds selected from the group consisting of alcohols, ethers, esters, ketones, nitromethane, and halogenated hydrocarbons.
  • the preferred alcohols and halogenated hydrocarbons contain from 1 to 4 carbon atoms; the preferred ethers contain from 2 to 4 carbon atoms; and the preferred esters and ketones contain from 3 to 4 carbon atoms.
  • suitable alcohols include methanol, ethanol and isopropanol.
  • suitable ethers include tetrahydrof ran.
  • suitable ketones include acetone.
  • Suitable halogenated hydrocarbons include methylene chloride, 1,1,2-trichloro-l,2,2-trifluoroethane, dichlorodifluoroethane and trans-l,2-dichloroethylene.
  • methylene chloride 1,1,2-trichloro-l,2,2-trifluoroethane, dichlorodifluoroethane and trans-l,2-dichloroethylene.
  • such compositions contain at least about 5 percent by weight of C456ff; and can contain up to 95 percent by weight, or even more of C456ff.
  • Most preferred with respect to ozone depletion potential are compositions in which all components contain no chlorine.
  • compositions which comprise an admixture of effective amounts of C456ff and one or more solvents selected from the group consisting of alcohols, ethers, esters, ketones, nitromethane and halogenated hydrocarbons to form an azeotrope or azeotrope-like mixture, are considered especially useful.
  • Compositions which are mixtures of C456ff with alcohol selected from the group consisting of methanol and ethanol are preferred.
  • azeotrope or azeotrope-like constant boiling liquid admixtures of two or more substances which admixtures behave like a single substance in that the vapor produced by partial evaporation or distillation has the same composition as the liquid, i.e., the admixtures distill without a substantial change in composition.
  • Constant boiling compositions characterized as azeotropes or azeotrope-like exhibit either a maximum or minimum boiling point as compared with that of nonazeotropic mixtures of the same substances.
  • effective amounts is meant the amounts of each component of the admixture of the instant invention, which, when combined, results in the formation of the azeotrope or azeotrope-like admixture of the instant invention.
  • the composition may be defined as an azeotrope of its components, say component A and component B, since the very term "azeotrope" is at once both definitive and limitive, requiring that effective amounts of A and B form this unique composition of matter which is a constant boiling admixture. It is well known by those who are skilled in the art that at differing pressures, the composition of a given azeotrope will vary, at least to some degree, and changes in distillation pressures also change, at least to some degree, the distillation temperatures. Thus, an azeotrope of A and B represents a unique type of relationship but with a variable composition depending on temperature and/or pressure. Therefore, compositional ranges, rather than fixed compositions, are often used to define azeotropes.
  • composition can be defined as a particular weight relationship or mole percent relationship of A and B, while recognizing that such specific values point out only one particular such relationship and that in actuality a series of such relationships represented by A and B actually exist for a given azeotrope, varied by influence of distillative conditions of temperature and pressure.
  • the azeotropic series represented by A and B can be characterized by defining the composition as an azeotrope characterized by a boiling point at a given pressure, thus giving identifying characteristics without unduly limiting the scope of the invention by a specific numerical composition, which is limited by and is only as accurate as the analytical equipment available.
  • Azeotrope or azeotrope-like compositions are provided in accordance with this invention which comprise admixtures of effective amounts of C456ff with an alcohol selected from the group consisting of methanol and ethanol to form an azeotrope or azeotrope- like mixture.
  • compositions which are binary mixtures of from about 65 to 73 weight percent C 56ff and from about 27 to 35 weight percent methanol are characterized as azeotropes or azeotrope- like in that mixtures within this range exhibit a substantially constant boiling point. Being substantially constant boiling, the mixtures do not tend to fractionate to any great extent upon evaporation. After evaporation, only a small difference exists between the composition of the vapor and the composition of the initial liquid phase. This difference is so small that the compositions of the vapor and liquid phases are considered substantially identical. Accordingly, any mixture within this range exhibits properties which are characteristic of a true binary azeotrope.
  • compositions which are binary mixtures of from about 71 to 79 weight percent C456ff and from about 21 to 29 weight percent ethanol are characterized as an azeotrope or azeotrope-like in that mixtures within this range exhibit a substantially constant boiling point. Being substantially constant boiling, the mixtures do not tend to fractionate to any great extent upon evaporation.
  • any mixture within this range exhibits properties which are characteristic of a true binary azeotrope.
  • the binary composition consisting essentially of about 75 weight percent C456ff and about 25 weight percent ethanol has been established, within the accuracy of the fractional distillation method, as a true binary azeotrope, boiling at about 71°C at substantially atmospheric pressure and is the preferred azeotrope of this invention.
  • C456ff its azeotropes with methanol and ethanol, and other mixtures of this invention are useful in a wide variety of processes for cleaning solid surfaces which comprise treating said surface therewith.
  • Applications include removal of flux and flux residues from printed circuit boards contaminated therewith.
  • compositions of the invention may be used in conventional apparatus, employing conventional operating techniques.
  • the solvent(s) may be used without heat if desired, but the cleaning action of the solvent may be applied by conventional means (e.g. heating, agitation, etc.).
  • conventional means e.g. heating, agitation, etc.
  • ultrasonic irradiation it may be advantageous to use ultrasonic irradiation in combination with the solvent(s).
  • compositions provided in accordance with this invention can be used in cleaning processes such as is described in U.S. Patent No. 3,881,949 and U.S. Patent No. 4,715,900, both of which are incorporated herein by reference.
  • azeotropes and other mixtures of the instant invention can be prepared by any convenient method including mixing or combining the desired amounts of the components.
  • a preferred method is to weigh the desired amounts of each component and thereafter combine them in an appropriate container.
  • 1,2-dichlorohexafluorocyclopent-l-ene 100 g was added to a Parr bottle along with 5% palladium on carbon (2 g) , sodium acetate trihydrate (120 g) , and water (100 mL) .
  • the bottle was placed in a Parr shaker, purged several times with nitrogen, purged several times with hydrogen, and held under a hydrogen pressure of 60 psig for 24 hours with shaking.
  • the reaction mixture was then filtered to remove the catalyst and the organic layer was separated from the aqueous layer.
  • the yield of crude C456ff was 66 g, 96% of theory.
  • the crude product from several runs was combined, washed with water to remove acetic acid, and distilled. The pure product boiled at about 87 to 88°C.
  • EXAMPLE 3 25 grams of C456ff and 10 grams of methanol were combined and the mixture was distilled using a concentric tube column of the type commercially available from Ace Glass of Vineland, New Jersey. A constant boiling azeotrope was formed which had a boiling point of about 61.1°C. Gas chromatographic analysis showed the azeotrope consisted of 69.4% C456ff and 30.6% of methanol. EXAMPLE 4

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Abstract

Le composé 1,1,2,2,3,3-hexafluorocyclopentane et les mélanges dudit composé avec des alcools, des éthers, des esters, des cétones, du nitrométhane et des hydrocarbures halogénés sont décrits, ainsi qu'un procédé de nettoyage d'une surface solide qui consiste à traiter cette surface avec ledit composé ou lesdits mélanges. Des mélanges binaires de 1,1,2,2,3,3-hexafluorocyclopentane avec soit environ 27 à 35 % en poids de méthanol, soit environ 21 à 29 % en poids d'éthanol sont des compositions azéotropes ou du type azéotrope et sont particulièrement adaptés à l'utilisation lorsque la récupération et la réutilisation du solvant sont effectuées.
PCT/US1991/000470 1990-03-05 1991-01-30 1,1,2,2,3,3-hexafluorocyclopentane et son utilisation dans des compositions et des procedes de nettoyage WO1991013846A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48927590A 1990-03-05 1990-03-05
US489,275 1990-03-05

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WO1991013846A1 true WO1991013846A1 (fr) 1991-09-19

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993007308A1 (fr) * 1991-10-01 1993-04-15 E.I. Du Pont De Nemours And Company Compositions azeotropes de 1,1,1,2,3,4,4,5,5,5-decafluoropentane et trans-1,2,-dichloroethylene, cis-1,2-dichloroethylene ou 1,2-dichloroethane
WO1999006616A1 (fr) * 1997-07-30 1999-02-11 E.I. Du Pont De Nemours And Company Procede et solution de filage eclair
US6355113B1 (en) 1991-12-02 2002-03-12 3M Innovative Properties Company Multiple solvent cleaning system
EP4032533A1 (fr) 2012-07-10 2022-07-27 The Regents of The University of California Méthodes pour induire une anesthésie

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109219652A (zh) * 2016-04-04 2019-01-15 D·谢尔利夫 使用不可燃、共沸或类共沸的组合物清洗制品的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315783A1 (fr) * 1987-10-20 1989-05-17 Bayer Ag Procédé pour la préparation d'hydrocarbures fluorés en C-4 à C-6, hydrocarbures fluorés cycliques, ainsi que l'emploi d'hydrocarbures fluorés en C-4 à C-6 comme gaz propulsant et liquide pour systèmes de pompes à chaleur

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315783A1 (fr) * 1987-10-20 1989-05-17 Bayer Ag Procédé pour la préparation d'hydrocarbures fluorés en C-4 à C-6, hydrocarbures fluorés cycliques, ainsi que l'emploi d'hydrocarbures fluorés en C-4 à C-6 comme gaz propulsant et liquide pour systèmes de pompes à chaleur

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993007308A1 (fr) * 1991-10-01 1993-04-15 E.I. Du Pont De Nemours And Company Compositions azeotropes de 1,1,1,2,3,4,4,5,5,5-decafluoropentane et trans-1,2,-dichloroethylene, cis-1,2-dichloroethylene ou 1,2-dichloroethane
AU656102B2 (en) * 1991-10-01 1995-01-19 E.I. Du Pont De Nemours And Company Azeotropic compositions of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, CIS-1,2-dichloroethylene or 1,1-dichloroethane
US6355113B1 (en) 1991-12-02 2002-03-12 3M Innovative Properties Company Multiple solvent cleaning system
US5874036A (en) * 1996-03-08 1999-02-23 E. I. Du Pont De Nemours And Company Flash-spinning process
WO1999006616A1 (fr) * 1997-07-30 1999-02-11 E.I. Du Pont De Nemours And Company Procede et solution de filage eclair
EP4032533A1 (fr) 2012-07-10 2022-07-27 The Regents of The University of California Méthodes pour induire une anesthésie

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CN1054611A (zh) 1991-09-18
AU7225891A (en) 1991-10-10

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